Rofecoxib

Base Information

• Chemical Name: Rofecoxib
• CAS No.: 162011-90-7
• Deprecated CAS: 186912-82-3
• Molecular Formula: C17H14O4S
• Molecular Weight: 314.362
• European Community (EC) Number: 803-260-0
• NSC Number: 758705,720256
• UNII: 0QTW8Z7MCR
• DSSTox Substance ID: DTXSID2023567
• Nikkaji Number: J1.041.252H
• Wikipedia: Rofecoxib
• Wikidata: Q411412
• NCI Thesaurus Code: C1832
• Pharos Ligand ID: T7L1GHJLUDGF
• Metabolomics Workbench ID: 53413
• ChEMBL ID: CHEMBL122
• Mol file: 162011-90-7.mol

Synonyms:MK 0966;MK 966;MK-0966;MK-966;refecoxib;rofecoxib;Vioxx;Vioxx Dolor

Chemical Property of Rofecoxib

Chemical Property:

• Appearance/Colour: off-white (pale yellow) crystalline powder
• Vapor Pressure: 2.42E-13mmHg at 25°C
• Melting Point: 207 °C
• Refractive Index: 1.619
• Boiling Point: 577.6 °C at 760 mmHg
• Flash Point: 303.1 °C
• PSA: 68.82000
• Density: 1.333 g/cm³
• LogP: 3.63850
• Storage Temp.: Refrigerator
• Solubility.: DMSO: soluble5mg/mL, clear (warmed)
• Water Solubility.: 9mg/L(25 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 314.06128010
• Heavy Atom Count: 22
• Complexity: 556

Purity/Quality:

98% ^*data from raw suppliers

Vioxx ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
• Recent ClinicalTrials: Study of Rofecoxib and Prolonged Constant Infusion of Gemcitabine in the Polychemotherapy Treatment of Advanced NSCLC
• Recent EU Clinical Trials: A Randomized, Double-Blind, Placebo-Controlled, Parallel Group, Phase III Study with a Long-Term, Open-label Extension to Evaluate the Efficacy and Safety of TRM-201 (Rofecoxib) in Patients with Hemophilic Arthropathy
• Description: Rofecoxib ts a non-steroidal anti-inflammatory drug (NSAID) launched in Mexico, its first market, for the management of acute pain and the treatment of osteoarthritis (OA) and primary dysmenorrhea. Rofecoxib can be obtained by several different ways; one example is by arylation of a 4-bromofuranone with a phenylboronic acid under Suzuki conditions. Rofecoxib is a highly selective inhibitor of COX-2, the inducible isoform of cyclooxygenase and therefore exhibits a potent antiinflammatory activity without concomitant gastric or renal toxicities linked to the non-specific COX-1/2 inhibitors. In several clinical studies in patients with knee or hip osteoarthritis, Rofecoxib was evaluated at 12.5-50 mg doses once daily: it demonstrated efficacy for all primary and secondary endpoints at doses considerably weaker than those for classical non-specific NSAIDs, with good tolerance and less adverse effects. Selective COX-2 inhibitors potentially have a large spectrum of activity including new indications such as Alzheimer's disease, colorectal cancer, irritable bowel disease or urinary incontinence.
• Uses: A selective cyclooxygenase-2 (COX-2) inhibitor. Use as an anti-inflammatory, analgesic. antipsychotic Labeled Rizatriptan, intended for use as an internal standard for the quantification of Rizatriptan by GC- or LC-mass spectrometry. Rofecoxib has been used in high performance bioaffinity chromatography.
• Indications: Rofecoxib is approved for the treatment of osteoarthritis, dysmenorrhea, and acute pain. The most common adverse reactions to rofecoxib are mild to moderate GI irritation (diarrhea, nausea, vomiting, dyspepsia, abdominal pain). Lower extremity edema and hypertension occur relatively frequently (about 3.5%). It is not metabolized by CYP2C9, so rofecoxib should not be subject to some of the interactions seen with celecoxib. However, its metabolism is increased by the coadministration of rifampin, which acts as a nonspecific inducer of hepatic metabolism.
• Clinical Use: Rofecoxib was indicated for the relief of the signs and symptoms of osteoarthritis, for the management of acute pain in adults, and for the treatment of primary dysmenorrhea.

Technology Process of Rofecoxib

There total 28 articles about Rofecoxib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-(4-(methylthio)phenyl)-3-phenylfuran-2(5H)-one (162012-30-8) → rofecoxib (162011-90-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; at 0 - 21 ℃;

DOI:10.1016/S0040-4039(99)01995-4

Reference yield: 95.0%

2-(4-methanesulfonylphenyl)-2-oxoethyl 2-(diethoxyphosphoryl)-2-phenylacetate → rofecoxib (162011-90-7)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 - 30 ℃; for 2h; Inert atmosphere;

DOI:10.1080/00397911.2011.577923

Reference yield: 94.0%

phenylacetic acid (103-82-2) + ethyl bromoacetate (105-36-2) → rofecoxib (162011-90-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; ethyl acetate;

upstream raw materials:

4-(4-(methylthio)phenyl)-3-phenylfuran-2(5H)-one

phenylacetic acid

2-bromo-1-(4-methanesulfonylphenyl)ethanone

3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one

Refernces

• 1、 Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min. "Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions". supporting information. p. 433 - 438. Retrieved 2020/02/13.
• 2、 -. "PURIFIED FORMS OF ROFECOXIB, METHODS OF MANUFACTURE AND USE". Paragraph 0069; 0081; 0334-0340; 0365-0387; 0394-0400. . Retrieved 2020/06/10.